Greek islands

Do Naxos OR Milos, not both... otherwise you will waste the equivalent of 24-36 hours in just transferring/ waiting for ferries/ getting on & off & getting to new hotel etc. VERY bad strategy. Because Milos has a very lame bus system and thus u would have to rent a car and drive your kids every time they wanted to do something, I would recommend Naxos instead. You could stay at St. George beach directly adjacent to Naxos Town (the port), so if your teens wanted to stroll into town & check out the Waffle House (main teen hangout) and video game places, you could just wave goodbye and say, be back by (whatever). One could carry a smartphone so you could be in touch, if you are a worry-worry type of parent. St. George beach is shallow, but also has water-sports center, Flisvos, whre they could rent kayaks sunfish, windsurf stuff etc. Also, they can take a bus that runs right along the shore to 3 other beaches -- Ag Prokopios, Ag anna and Plaka. St. George is about a 10-minute walk to all the attractions of the port town -- shops, cafes, museums, ancient ruins etc etc. On one day, the family could rent a car and zoom all over the island -- mountains made of marble, ancient statues in orchards, places for hiking, farms and vineyards. By contrast, In Milos you'd have to drive almost everywhere.

Another option would be to consider Star Clipper Cruises, they are a sailing ship out of Athens that does a week long circuit of the Greek islands. The four masted ships are fun and there's something about wind power that makes the trip even more of an adventure.

You do not have sufficient time to do three islands plus Athens. Whiole distances are short in Greece the fact that you are going t have to use ferries means you are tied to their schedules which will cost you a half day every time you hop thus Jans math 24 to 36 hours wasted on your 8 day trip.

I am pretty sure there are no direct flights Denmark to Naxos. Its runway is short so only small 45 seat turboprop aircraft service the island 9Mylos too). You will have to fly to Athens then connect to your island.

If you want to do Santorini there are lots of flights there in the evening so chances are you can catch a connecting flight on the day of your arrival. So do Santorini first. My budget can only stand 3 nights there then either ferry to Milos or Naxos you need to choose. Milos is lovely but yo have to have a car and in June anyway its still pretty quiet.
Naxos is much bigger with much better tourist infrastructure great beaches and a lovely main town. If it were me I would ferry to Naxos and stay 3 or 4 nights then fly back to Athens at least the day before your return flight.
Here is what you will see.
Naxos Town http://www.flickr.com/photos/stanbr54/sets/72157632094558042/
Trip around Naxos http://www.flickr.com/photos/stanbr54/sets/72157634605629689/

Milos 2011 http://www.flickr.com/photos/stanbr54/sets/72157632109429236/
Milos 2013 http://www.flickr.com/photos/stanbr54/sets/72157634779985764/

I also think you need to cut one Island and that Milos would be the obvious one. Santorini is strikingly beautifull but also crowded. However most of the selfie stick swinging Instagram crowd tend to stay around the caldera and leave the amazing ruins of Akrotiri and Ancient Thira to the more cultured among us.

I agree with Janet and stanbr. Just do two islands (Santorini and Naxos). I'd spend 2 nights Santorini, 4 nights Naxos.

Fly to Santorini, ferry to Naxos, then ferry or fly back to Athens.

There's plenty to do on Naxos to keep you busy. If you need a diversion, you could take a day trip to Mykonos and see Delos. Or take a little boat trip around the Small Cyclades.

By the way, the Flisvos Sports Center on Naxos has a hotel too, with a restaurant, with a great front "porch" to watch the sunset.

Thank you all so much. This is such a great help!

I think we'll drop Milos, and just do Santorini, Naxos and Athens.

I'm sure I'll be back with more questions as we continue to plan. :)

Hello,

I just wanted to say that Milos is an amazing island and you going to miss a lot if you don't visit. It has more than 70 beaches, all of unique beauty. I would suggest if you visit Greece again sometime to combine Milos with Serifos, Sifnos and Amorgos. Naxos is a great island for families, but the beaches look almost identical. Also, the Chora is not the characteristic cycladic style. Too many stores and full of people during high season, you cannot get the best out of this trip when the island is packed. Generally, next time you visit Greece you might like to try it at the end of Juny or early September ;)